3-Aminobenzonitrile → 4-(3-Cyanophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

HRID 2113566Notes

Reaction equation

HRID 2113566 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[NH2:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20]>>[C:19]([C:18]1[CH:17]=[C:16]([NH:15][C:2]2[C:11]3[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:13]#[N:14])[CH:23]=[CH:22][CH:21]=1)#[N:20]

Participants

3

Reactant 2

HCID 167023-AminobenzonitrileHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 691852384-(3-Cyanophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrileYield 29.1%

Procedure

Following the procedure described above in Example 13, 4-chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.300 g, 1.45 mmol) was reacted with 3-aminobenzonitrile (0.188 g, 1.59 mmol). The crude product was purified by flash chromatography over silica gel (15-30% EtOAc in CH2Cl2) to give pure 4-(3-cyanophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.122 g, 29% yield): 1H NMR (400 MHz, DMSO-D6) δ 7.57-7.80 (m, 3 H) 7.88 (s, 1 H) 8.16 (s, 1 H) 8.75 (s, 1 H) 9.11 (s, 1 H) 10.23 (s, 1 H).

Workup

  1. customThe crude product was purified by flash chromatography over silica gel (15-30% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-b7fdadd626af4e21b317f5ac22bb1a70
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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